Title: Pleasant Valley Vacation Packages & Trips 2026 from CA $540 | Expedia.ca [Hotels in Pleasant Valley](https://expedia.ca/Pleasant-Valley-Hotels.d6046250.Travel-Guide-Hotels)[Vacation Rentals in Pleasant Valley](https://expedia.ca/Pleasant-Valley-Vacation-Rentals.d6046250.Travel-Guide-VacationRentals)[Things to do in Pleasant Valley](https://expedia.ca/Things-To-Do-In-Pleasant-Valley.d6046250.Travel-Guide-Activities)[Pleasant Valley Car Rentals](https://expedia.ca/Car-Rentals-In-Pleasant-Valley.d6046250.Car-Rental-Guide) ![](https://images.trvl-media.com/place/6046250/2171ebd9-dd8f-4602-b20a-452a2bb91ee1.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Pleasant Valley Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to CA $1,096 when you book a flight and hotel together\* - ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package - ### Rest easy Plan, book, and manage your trip all in one place #### Your Pleasant Valley Vacation The hassle-free way to experience this interesting city is with a tailor-made Pleasant Valley vacation package. Stay in the neighborhood of Poughkeepsie Waterfront, which is great for families, history and culture or choose someplace else — our packages are all about you. If your trip to Pleasant Valley includes some sightseeing, visit renowned attractions like [Marist College](https://www.expedia.ca/Marist-College-Poughkeepsie.d6158002.Vacation-Attraction), [Vassar College](https://www.expedia.ca/Vassar-College-Poughkeepsie.d6085394.Vacation-Attraction) and [Culinary Institute of America](https://www.expedia.ca/Culinary-Institute-Of-America-Hyde-Park.d6093745.Vacation-Attraction). Whatever your travel plans or the size of your budget, putting together the ultimate tailored Pleasant Valley vacation is easy with Expedia. ## Top Pleasant Valley Vacation Deals Price found within the past 48 hours. Click for updated prices. ![Courtyard by Marriott Newburgh Stewart Airport](https://images.trvl-media.com/lodging/1000000/50000/42700/42673/7494afa4_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Courtyard by Marriott Newburgh Stewart Airport CA $540 per person Apr 27 - Apr 30 found 19 hours ago Roundtrip flight included Toronto (YTO) to Newburgh (SWF) 8.2/10 Very Good! (712 reviews) Older room with chemical cleaning solution smell Reviewed on Mar 24, 2026 ![Sleep Inn & Suites Middletown - Goshen](https://images.trvl-media.com/lodging/17000000/16710000/16700200/16700177/aeade474_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Sleep Inn & Suites Middletown - Goshen CA $718 per person May 8 - May 11 found 1 day ago Roundtrip non-stop flight included Calgary (YYC) to Newburgh (SWF) 8.6/10 Excellent! (1,015 reviews) Clean room, safe and staff is courteous Reviewed on Mar 19, 2026 ![Super 8 by Wyndham Newburgh/West Point Near Stewart Airport](https://images.trvl-media.com/lodging/1000000/460000/459800/459793/b66016e5_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Super 8 by Wyndham Newburgh/West Point Near Stewart Airport CA $913 per person May 17 - May 23 found 6 hours ago Roundtrip flight included Vancouver (YVR) to Newburgh (SWF) 5.4/10 (1,003 reviews) Staffs were extremely kind. Reviewed on Jan 4, 2026 ![La Quinta Inn & Suites by Wyndham Middletown-Goshen](https://images.trvl-media.com/lodging/1000000/10000/4100/4098/26de74c3_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### La Quinta Inn & Suites by Wyndham Middletown-Goshen CA $787 per person May 9 - May 12 found 1 day ago Roundtrip non-stop flight included Calgary (YYC) to Newburgh (SWF) 9.4/10 Exceptional! (985 reviews) Best hotel in town. Clean clean smoke free hotel Reviewed on Feb 27, 2026 ![The Lagrange Inn & Extended Stay](https://images.trvl-media.com/lodging/107000000/106020000/106017000/106016996/f805fd7d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Lagrange Inn & Extended Stay CA $733 per person May 8 - May 11 found 1 day ago Roundtrip non-stop flight included Calgary (YYC) to Newburgh (SWF) 9.4/10 Exceptional! (13 reviews) The room was freezing cold for about a half hour when we got there but the heater worked well and eventually it warmed up. Room was large and clean. Parking was right in front of room. Wish the room had a full length mirror. People travel when they have an event to go to and we like to see how we look. The bathroom mirror sort of tilts down for a bit of an outfit check but a full length would have been great. Bed was comfortable and bedding was really nice! Guy who runs the place was very nice! Easy check in with digital code and no need for a front desk visit. We would stay again if in the area. Reviewed on Jan 8, 2026 ## Ready to book your vacation to Pleasant Valley? Choose your dates ## Pleasant Valley Hotel Deals ![Best Western Plus Kingston Hotel And Conference Center](https://images.trvl-media.com/lodging/1000000/10000/6100/6056/d26fbbb0_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Best Western Plus Kingston Hotel And Conference Center 503 Washington Ave Kingston NY Fully refundableReserve now, pay when you stay CA $164 CA $184 total Apr 7 - Apr 8 includes taxes & fees 7.6/10 Good! (1,004 reviews) There was a mystery pill found on the floor in the room. Lucky my dog didnt eat it. Still taking him to the vet. The hotel staff had nothing to say about it and even tried to take away the evidence. Also, anyone can walk in and wander around. Doors open without a key. Reviewed on Mar 23, 2026 [](https://expedia.ca/Hotel-Search?startDate=07%2F04%2F2026&endDate=08%2F04%2F2026&selected=6056&PinnedHotelID=6056&HadPinnedHotel=true®ionId=6046250) ![Hampton Inn & Suites Poughkeepsie](https://images.trvl-media.com/lodging/2000000/1930000/1927100/1927088/ee108dad_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hampton Inn & Suites Poughkeepsie 2361 South Rd Poughkeepsie NY Fully refundableReserve now, pay when you stay CA $160 CA $185 total Apr 10 - Apr 11 includes taxes & fees 9/10 Wonderful! (1,000 reviews) Clean room with comfortable bed and nice bathroom. Friendly staff. Reviewed on Mar 23, 2026 [](https://expedia.ca/Hotel-Search?startDate=10%2F04%2F2026&endDate=11%2F04%2F2026&selected=1927088&PinnedHotelID=1927088&HadPinnedHotel=true®ionId=6046250) ![Wildflower Farms, Auberge Collection](https://images.trvl-media.com/lodging/80000000/79880000/79873100/79873064/2028d4aa_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Wildflower Farms, Auberge Collection 2702 Main St Gardiner NY CA $1,548 CA $1,809 total Apr 13 - Apr 14 includes taxes & fees [](https://expedia.ca/Hotel-Search?startDate=13%2F04%2F2026&endDate=14%2F04%2F2026&selected=79873064&PinnedHotelID=79873064&HadPinnedHotel=true®ionId=6046250) [See all 1,094 properties in Pleasant Valley](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=27%2F03%2F2026&endDate=28%2F03%2F2026®ionId=6046250) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ## Explore a world of travel with Expedia \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app